Chelsea Boots made their first footprint (no pun intended) on popular coolness as part of 1960s Mod style, and nothing in the intervening years has made the formula less desireable. These clean-lined boots look particularly good with suits or dress trousers, and the elastic gussets serve a purpose besides just being easy to pull on and off—the absence of laces means nothing to interfere with the break of your carefully placed hem. A few options at different price points, all available in both black and brown:

Lands' End Fulton [$159] — For the price, not a bad all-around piece of footwear. Leather sole and stacked heel. The best budget option so far.

Loake 290 [$240] — Very cool and classic boot. Made in England. Comes in an incomparably beautiful polished brown. Only downside: almost impossible to find in North American distribution, so expect hefty return shipping fees to Europe if you don't get your size right the first try.